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Lewis acid catalyzed acylation reactions: scope and limitations

Kusum L. Chandra, P. Saravan, Rajesh K. Singh and Vinod K. Singh*

*Department of Organic Chemistry, Indian Institute of Technology, Kanpur 208 016, India, Email: vinodksiitk.ac.in

K. L. Chandra, P. Saravan, R. K. Singh, V. K. Singh, Tetrahedron, 2002, 58, 1369-1374.

DOI: 10.1016/S0040-4020(01)01229-7 


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Abstract

Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu(OTf)2 was very efficient in catalyzing the reaction under mild conditions in CH2Cl2. The selectivity for acylation of primary or secondary alcohols over tertiary ones is discussed.

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proposed mechanism



Key Words

acylations, acetic acid esters, thioesters, alcohols, thiols, phenols, sugars, copper triflate, acetic anhydride


ID: J72-Y2002-1020